Benzyl 4-Hydroxybenzoate → Benzyl 4-(methoxycarbonylmethoxy)benzoate

Reaction equation

[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:25][C:26]([O:28][CH2:29]C)=[O:27]>CC(C)=O>[CH3:29][O:28][C:26]([CH2:25][O:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1)=[O:27]

Participants

Procedure

4.5 g (0.02 mol) of benzyl p-hydroxybenzoate were suspended in about 60 ml of acetone together with 9.7 g (0.03 mol) of cesium carbonate and treated with 2.3 ml (0.025 mol) of ethyl bromoacetate. The mixture was then refluxed until reaction was complete. For working-up, the reaction solution was filtered through a clarifying layer and the filtrate was concentrated to dryness. The residue was taken up in ethyl acetate and the mixture was washed three times each with 10% strength citric acid solution and saturated NaCl solution. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was recrystallized from diisopropyl ether/heptane. Yield: 5.5 g.